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Vacation rentals in Gaiole in Chianti

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Gaiole in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Poggio San Marco

4.97 out of 5 average rating, 232 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Dec 8 – 15

G$40,529 GYD per night
Guest favorite

Home in Gaiole in Chianti

4.95 out of 5 average rating, 205 reviews

"La Casa di Maria Luce"® with rooftop terrace

"La Casa di Maria Luce" ® Selvolini is located in the medieval village of Lecchi in Chianti (8 km from Gaiole) in the heart of Chianti Classico, equipped with large spaces, can comfortably accommodate 4-5 people. It consists of kitchen-living room, 2 nice bedrooms, 2 full bathrooms. 50 meters away. Grocery store for basic necessities, tobacco shops, a bar-room for breakfast and quick lunches, a great restaurant a few steps from the house. The large equipped terrace offers a nice view of the countryside.

Aug 15 – 22

G$27,101 GYD per night
Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 103 reviews

Villa di Geggiano - Guesthouse

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Jan 18 – 25

G$104,806 GYD per night

Popular amenities for Gaiole in Chianti vacation rentals

Stay near Gaiole in Chianti's top sights

Castello di Spaltenna4 locals recommend
I'GALLETTO BRIACO6 locals recommend
Lo Sfizio6 locals recommend
Coop Informa6 locals recommend
Il Ristorante Il Pievano4 locals recommend
Enoteca La Cantinetta Del Chianti S.A.S. Di Azzato Riccardo Michele8 locals recommend

Other great vacation rentals in Gaiole in Chianti

Guest favorite

Apartment in Cavriglia

4.96 out of 5 average rating, 120 reviews

ABOVE the HAZE tourist rental

Jul 10 – 17

G$13,232 GYD per night
Superhost

Condo in Montevarchi

4.94 out of 5 average rating, 175 reviews

Art-Design Fienile in the heart of Tuscany

Sep 5 – 12

G$18,618 GYD per night
Guest favorite

Villa in Ambra

4.98 out of 5 average rating, 107 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Mar 16 – 23

G$175,223 GYD per night
Guest favorite

Farm stay in Greve in Chianti

4.96 out of 5 average rating, 162 reviews

Le Balze di Pile Farmhouse - Greve in Chianti

Mar 25 – Apr 1

G$26,744 GYD per night
Guest favorite

Condo in Gaiole In Chianti

4.93 out of 5 average rating, 14 reviews

Transit Divino Gaiole

May 30 – Jun 6

G$20,011 GYD per night
Superhost

Cottage in Gaiole In Chianti

4.82 out of 5 average rating, 96 reviews

Old Chianti chapel-style cottage

Jan 27 – Feb 3

G$31,201 GYD per night
Guest favorite

Farm stay in Gaiole In Chianti

4.98 out of 5 average rating, 88 reviews

Villa Le Miccine w/ Pool - Bello Fresco Unit for 2

Oct 18 – 25

G$59,093 GYD per night
Superhost

Home in Gaiole In Chianti

4.86 out of 5 average rating, 7 reviews

Casina del Chianti

Nov 5 – 12

G$21,228 GYD per night
Guest favorite

Farm stay in Radda In Chianti

4.96 out of 5 average rating, 78 reviews

Farmhouse in Chianti Heart with private lake B

Dec 27 – Jan 3

G$23,130 GYD per night
Guest favorite

Condo in Gaiole in Chianti

4.95 out of 5 average rating, 42 reviews

Casa Adele in Gaiole

Jul 13 – 20

G$16,816 GYD per night
Guest favorite

Apartment in Radda in Chianti

4.9 out of 5 average rating, 51 reviews

La Casina

Jan 15 – 22

G$21,043 GYD per night
Guest favorite

Villa in Gaiole In Chianti

5.0 out of 5 average rating, 31 reviews

Sestuccia

Dec 28 – Jan 4

G$175,510 GYD per night

Quick stats about vacation rentals in Gaiole in Chianti

Total rentals

40 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

810 reviews

Nightly prices starting at

G$8,375 GYD before taxes and fees

Frequently Asked Questions

  • How much does it cost to stay in condo rentals in Gaiole in Chianti?

    Experience the best of Gaiole in Chianti with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Gaiole in Chianti?

    Yes! Work meets play with ease at over 10 vacation rentals in Gaiole in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Gaiole in Chianti apartment rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 apartment rentals with pools in Gaiole in Chianti, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Gaiole in Chianti have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Gaiole in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Gaiole in Chianti?

    Four-legged friends are welcome in Gaiole in Chianti. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Gaiole in Chianti?

    Gaiole in Chianti has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Gaiole in Chianti